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Synlett 2023; 34(03): 211-220
DOI: 10.1055/a-1970-4290
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Recent Progress towards the Transition-Metal-Catalyzed Dearomatizing Spirocyclization Reactions of Indolyl Ynones

Kua-Fei Wei
a   College of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
,
Xiao-Lei Jiang
a   College of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
b   Sanmenxia Polytechnic, Sanmenxia, Henan 472000, P. R. of China
,
Guang-Xin Ru
a   College of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
,
Xiu-Hong Zhu
a   College of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
,
Wen-Bo Shen∗
a   College of Sciences and College of Forestry, Henan Agricultural University, Zhengzhou 450002, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the NNSFC (22001059), the Top-Notch Talents Program of Henan Agricultural University (30500739).
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Abstract

Dearomatizing spirocyclization reactions are very appealing synthetic strategies to generate functionalized three-dimensional scaffolds from simple two-dimensional precursors. Recently, the field of transition-metal-catalyzed dearomatizing spirocyclization reactions of indolyl ynones has burgeoned, as the construction of synthetically challenging quaternary spirocyclic carbons is easily achieved. In this review, we introduce an overview of advances in the transition-metal-catalyzed dearomatizing spirocyclization reactions of indolyl ynones, with the reactions being categorized according to type of catalyst.

Key words

transition-metal catalysis - indolyl ynones - dearomatization - spirocyclization - spirocyclic indolenines


Publication History

Received: 17 October 2022

Accepted after revision: 30 October 2022

Accepted Manuscript online:
30 October 2022

Article published online:
06 December 2022

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  • References and Notes


      • For selected examples, see:
    • 1a Liu C.-T, Wang Q.-W, Wang C.-H. J. Am. Chem. Soc. 1981; 103: 4634
      Crossref
    • 1b Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
      Crossref
    • 1c Jadulco R, Edrada RA, Ebel R, Berg A, Schaumann K, Wray V, Steube K, Proksch P. J. Nat. Prod. 2004; 67: 78
      CrossrefPubMed
    • 1d Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
      CrossrefPubMed
    • 1e Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
      CrossrefPubMed
    • 1f Zhou X.-J, Liu H.-Y, Mo Z.-Y, Ma X.-L, Chen Y.-Y, Tang H.-T, Pan Y.-M, Xu Y.-L. Chem. Asian J. 2020; 15: 1536
      CrossrefPubMed
    • 2a Zheng C, You S.-L. Acc. Chem. Res. 2020; 53: 974
      PubMed
    • 2b Varlet T, Matišić M, Elslande EV, Neuville L, Gandon V, Masson G. J. Am. Chem. Soc. 2021; 143: 11611
      CrossrefPubMed
    • 2c Nie Y.-H, Komatsuda M, Yang P, Zheng C, Yamaguchi J, You S.-L. Org. Lett. 2022; 24: 1481
      CrossrefPubMed
    • 2d Becker A, Grugel CP, Breit B. Org. Lett. 2021; 23: 3788
      CrossrefPubMed
    • 2e Sabat N, Soualmia F, Retailleau P, Benjdia A, Berteau O, Guinchard X. Org. Lett. 2020; 22: 4344
      CrossrefPubMed
    • 2f Wu Q.-F, He H, Liu W.-B, You S.-L. J. Am. Chem. Soc. 2010; 132: 11418
      CrossrefPubMed
    • 2g Zhang Y.-Q, Chen Y.-B, Liu J.-R, Wu S.-Q, Fan X.-Y, Zhang Z.-X, Hong X, Ye L.-W. Nat. Chem. 2021; 13: 1093
      CrossrefPubMed
    • 3a Zhang B, Li X, Ai Z, Zhao B, Yu Z, Du Y. Org. Lett. 2022; 24: 390
      CrossrefPubMed
    • 3b Ho HE, Pagano A, Rossi-Ashton JA, Donald JR, Epton RG, Churchill JC, James MJ, O’Brien P, Taylor RJ. K, Unsworth WP. Chem. Sci. 2020; 11: 1353
      CrossrefPubMed

      For selected reviews, see:
    • 4a Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res. 2014; 47: 2558
      CrossrefPubMed
    • 4b Liebov BK, Harman WD. Chem. Rev. 2017; 117: 13721
      CrossrefPubMed
    • 4c Remy R, Bochet CG. Chem. Rev. 2016; 116: 9816
      CrossrefPubMed
    • 4d Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
      CrossrefPubMed
    • 4e Ortiz FL, Iglesias MJ, Fernández I, Sánchez CM. A, Gómez GR. Chem. Rev. 2007; 107: 1580
      CrossrefPubMed
    • 4f Pape AR, Kaliappan KP, Kündig EP. Chem. Rev. 2000; 100: 2917
      CrossrefPubMed

      For selected reviews, see:
    • 5a Zheng C, You S.-L. Acc. Chem. Res. 2020; 53: 974
      CrossrefPubMed
    • 5b Zheng C, You S.-L. ACS Cent. Sci. 2021; 7: 432
      CrossrefPubMed
    • 5c Saya JM, Ruijter E, Orru RV. A. Chem. Eur. J. 2019; 25: 8916
      CrossrefPubMed
    • 5d Roche SP, Tendoung J.-JY. Tréguier B. Tetrahedron 2015; 71: 3549
      Crossref

      For selected reviews, see:
    • 6a Zheng Z, Ma X, Cheng X, Zhao K, Gutman K, Li T, Zhang L. Chem. Rev. 2021; 121: 8979
      CrossrefPubMed
    • 6b Zhang L. Acc. Chem. Res. 2014; 47: 877
      CrossrefPubMed
    • 6c Yeom H.-S, Shin S. Acc. Chem. Res. 2014; 47: 966
      CrossrefPubMed
    • 6d Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
      CrossrefPubMed
    • 6e Qian D, Zhang J. Chem. Soc. Rev. 2015; 44: 677
      CrossrefPubMed
    • 6f Ye L.-W, Zhu X.-Q, Sahani RL, Xu Y, Qian P.-C, Liu R.-S. Chem. Rev. 2021; 121: 9039
      CrossrefPubMed
    • 6g Shen W.-B, Tang X.-T. Org. Biomol. Chem. 2019; 17: 7106
      CrossrefPubMed
    • 6h Ru G.-X, Zhang T.-T, Zhang M, Jiang X.-L, Wan Z.-K, Zhu X.-H, Shen W.-B, Gao G.-Q. Org. Biomol. Chem. 2021; 19: 5274
      CrossrefPubMed
    • 6i Gao G.-Q, Ma G, Jiang X.-L, Liu Q, Fan C.-L, Lv D.-C, Su H, Ru G.-X, Shen W.-B. Org. Biomol. Chem. 2022; 20: 5035
      CrossrefPubMed
    • 6j Tang X.-T, Yang F, Zhang T.-T, Liu Y.-F, Liu S.-Y, Su T.-F, Lv D.-C, Shen W.-B. Catalysts 2020; 10: 350
      Crossref
    • 7a Fedoseev P, Coppola G, Ojeda GM, Eycken EV. V. Chem. Commun. 2018; 54: 3625
      CrossrefPubMed
    • 7b Fedoseev P, Eycken EV. Chem. Commun. 2017; 53: 7732
      CrossrefPubMed
    • 7c Han G, Xue L, Zhao L, Zhu T, Hou J, Song Y, Liu Y. Adv. Synth. Catal. 2019; 361: 678
      Crossref

      For selected examples, see:
    • 8a Shen W.-B, Tang X.-T, Zhang T.-T, Lv D.-C, Zhao D, Su T.-F, Meng L. Org. Lett. 2021; 23: 1285
      CrossrefPubMed
    • 8b Shen W.-B, Zhang T.-T, Zhang M, Wu J.-J, Jiang X.-L, Ru G.-X, Gao G.-Q, Zhu X.-H. Org. Chem. Front. 2021; 8: 4960
      CrossrefPubMed
    • 8c Shen W.-B, Tang X.-T, Zhang T.-T, Liu S.-Y, He J.-M, Su T.-F. Org. Lett. 2020; 22: 6799
      CrossrefPubMed
    • 8d Zheng Y, Zhang T.-T, Shen W.-B. Org. Biomol. Chem. 2021; 19: 9688
      CrossrefPubMed
    • 8e Zhang T.-T, Wei K.-F, Ru G.-X, Zhu X.-H, Xie L.-X, Shen W.-B. Synlett 2022; in press DOI: 10.1055/a-1957-4104.
      Article in Thieme Connect
  • 9 James MJ, Cuthbertson JD, O’Brien P, Taylor RJ. K, Unsworth WP. Angew. Chem. Int. Ed. 2015; 54: 7640
    CrossrefPubMed
  • 10 Clarke AK, James MJ, O’Brien P, Taylor RJ. K, Unsworth WP. Angew. Chem. Int. Ed. 2016; 55: 13798
    CrossrefPubMed

      • For Ag-NPs in catalysis, see:
    • 11a Bhosale MA, Bhanage BM. Curr. Org. Chem. 2015; 19: 708
      Crossref
    • 11b Cong H, Porco JA. ACS Catal. 2012; 2: 65
      CrossrefPubMed
    • 11c Shimizu K.-I, Sato R, Satsuma A. Angew. Chem. Int. Ed. 2009; 48: 3982
      CrossrefPubMed
    • 11d Mitsudome T, Arita S, Mori H, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2008; 47: 7938
      CrossrefPubMed
    • 11e Qi C, Qin T, Suzuki D, Porco JA. J. Am. Chem. Soc. 2014; 136: 3374
      CrossrefPubMed
  • 12 Liddon JT. R, Clarke AK, Taylor RJ. K, Unsworth WP. Org. Lett. 2016; 18: 6328
    CrossrefPubMed
  • 13 Liddon JT. R, Rossi-Ashton JA, Clarke AK, Lynam JM, Taylor RJ. K, Unsworth WP. Synthesis 2018; 50: 4829
    Article in Thieme ConnectPubMed
  • 14 Ho HE, Stephens TC, Payne TJ, O’Brien P, Taylor RJ. K, Unsworth WP. ACS Catal. 2019; 9: 504
    CrossrefPubMed

      • For prominent examples of the use of Pd-catalysis in dearomatizing spirocyclization, see:
    • 15a Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc. 2005; 127: 4592
      CrossrefPubMed
    • 15b Rousseaux S, García-Fortanet J, Del Aguila Sanchez MA, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 9282
      CrossrefPubMed
    • 15c Wu K.-J, Dai LX, You S.-L. Org. Lett. 2012; 14: 3772
      CrossrefPubMed
    • 15d Montgomery TD, Nibbs AE, Zhu Y, Rawal VH. Org. Lett. 2014; 16: 3480
      CrossrefPubMed
    • 15e Gao S, Wu Z, Fang X, Lin A, Yao H. Org. Lett. 2016; 18: 3906
      CrossrefPubMed
    • 15f Hu W, Wang H, Bai L, Liu J, Luan X. Org. Lett. 2018; 20: 880
      CrossrefPubMed
  • 16 Liddon JT. R, James MJ, Clarke AK, O’Brien P, Taylor RJ. K, Unsworth WP. Chem. Eur. J. 2016; 22: 8777
    CrossrefPubMed
  • 17 Li C, Xue L, Zhou J, Zhao Y, Han G, Hou J, Song Y, Liu Y. Org. Lett. 2020; 22: 3291
    CrossrefPubMed
    • 18a Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
      CrossrefPubMed
    • 18b Meanwell NA. J. Med. Chem. 2018; 61: 5822
      CrossrefPubMed
    • 18c Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
      CrossrefPubMed
    • 18d Wang J, Sánchez-Roselló M, Aceña JL, Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
      CrossrefPubMed
  • 19 Inprung N, Ho HE, Rossi-Ashton JA, Epton RG, Whitwood AC, Lynam JM, Taylor RJ. K, James MJ, Unsworth WP. Org. Lett. 2022; 24: 668
    CrossrefPubMed
  • 20 Ru G.-X, Zhang M, Zhang T.-T, Jiang X.-L, Gao G.-Q, Zhu X.-H, Wang S, Fan C.-L, Li X, Shen W.-B. Org. Chem. Front. 2022; 9: 2621
    CrossrefPubMed